


A Series of Firsts

by WeirdItalianPlumber



Category: It's Always Sunny in Philadelphia
Genre: A series of oneshots, Drug Use, F/M, First Kiss, First Time, It’ll probably be a mix of shippy and platonic, I’ll add more tags as chapters go up
Language: English
Status: In-Progress
Published: 2018-05-09
Updated: 2018-06-10
Packaged: 2019-05-04 14:33:06
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,733
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14595090
Author URL: https://archiveofourown.org/users/WeirdItalianPlumber/pseuds/WeirdItalianPlumber
Summary: One-shots of significant moments in the lives of Dee Reynolds and Charlie Kelly, and the firsts they share together.





	1. First Kiss

**Author's Note:**

> Takes place around 1996. The gang are 20 years old. They're all hanging out when Dennis and Dee come home for spring break.

**Notes for the Chapter:**

> Takes place around 1996. The gang are 20 years old. They're all hanging out when Dennis and Dee come home for spring break.

"I look  _good_ ," Dee brags, striking a pose before the line of three men before her. She had finally gotten rid of her backbrace for good, and was excited to show everyone.  

Mac is the first to respond, snorting a "No." 

Dennis joins in. He’s already seen the big reveal, but isn’t going to pass up an opportunity to be a dick. Especially in front of Mac. "You look worse, actually. All that metal hid those gangly limbs." 

Dee rolls her eyes. "Whatever. I don't care what you two losers think.  _Real men_  think I'm hot."  

Charlie can't understand what problems they saw; Dee's tall and thin and fit the description of those girls everyone seemed to lust over. Okay, she has smaller boobs than ideal, and she's pretty loud and kind of mean. But, she also can outdrink most people and isn't afraid of anyone. Which is pretty sweet.  

He hears Dennis say something back but doesn't process what. He's used to blocking out the twins' arguing. It's a common occurrence. The only thing worse than their arguing with each other is when they team up- getting on the same superior page. 

There's a high-pitched sound of frustration, and Dee stomps off. Charlie follows; being around a pissy Dee was preferable to watching Mac and Dennis try to get all macho. 

"Ugh, I should've seen if The Rat had any weed first," Dee says when she stops to lean against the wall to the Reynolds' house. "I swear it's the only way I can deal with him." 

Charlie wants to defend his friend, but he also doesn't want to piss Dee off. Not after just reconnecting again. While everything felt calm and normal, still.  

"They have a bunch of beer back there we could be drinking. If you didn't have to get so bitchy about it," he mutters, like she was the problem.  

It seems he’s struck a nerve anyway. Her eyes get huge, nearly popping out of her head. It's something Charlie should probably insult her for, but it's just the two of them and it's not so much fun when there's no one around to praise him for it. Also, they’re the same shade of blue as the local diving pool he loved, and it’s a little distracting.   

"They started it," she practically yells. "Is it that hard for them to say something nice?"  

Charlie doesn't respond. The guys were being mean, he agrees, but Dee is at fault, too, having expected anything different from them. He doesn’t think she was looking for a real answer, anyway.  

"You haven't said anything, yet. What do you think?"  Dee displays herself in front of him. There’s a sense of pride, but after years of friendship, Charlie can easily pick out her vulnerability. 

Honestly, he isn’t sure what to think. Dee isn’t dressed like most people. She’s wearing the same baggy jeans as everyone else. But instead of oversized sweaters, she’s in a short shirt showing her midriff.  He prefers that cute girl whose name he always forget’s modest and simple style.  

Dee seems to be making a big deal out of this. He didn't think she looked so bad before, anyway. 

Charlie avoids a direct answer. “Yeah, it’s cool. I know you’ve been waiting for this.” Either she’s egotistical enough to hear what she wants, or her standards for receiving a compliment are that low, but she seems happy with that response.  

"I missed this," Dee comments, "just us hanging out." College isn't like she had been expecting. Parties are great, but there's something about sitting around drinking and arguing with friends that can't be replaced.  

Charlie simply shrugs, kicking at some dirt. He kind of did, too. He looks up at her, somehow expressing a mixture of cluelessness and sincerity. He starts grinning at her, even though he’s not sure why.  

She considers Charlie for a moment. Looks at his green eyes shining in the sunlight, at the hint of freckles she always assumed was a permanent layer of dirt. He's no football star, but he has nice features. 

"Nobody ever finds out about this," Dee says. She steps forward and kisses him. Charlie almost jumps back, because this is Dee. Instead, he moves his lips against hers, because  _th_ _is is Dee._ She smells really good up close and her skin is soft where her hand rests on his face. The world seems to stop, and all he can think about is how surprised he is that he’s enjoying this. Kissing isn't as gross as he remembers; it's kind of wet, but there's a nice tingly feeling and her lips are sweet. He wants to lean them against the wall, feel the body that’s been hidden in a cage for years, to not have to focus on standing.  

As he’s thinking about just how to do that, Dee pulls away. That’s a good idea, he realizes, he could use some air, maybe they could reorient then. But instead of coming back for more, she smiles as if something weird didn't just happen.  

"C'mon," she nods her head in the direction they came from, "before those guys can drink all the beer." 

**Notes for the Chapter:**

> I had a little trouble finding good information on the style back then. 
> 
> I feel like Dee would wear skimpier (for lack of a better word) clothes once she got her backbrace off, after years of insults.


	2. First Time

**Notes for the Chapter:**

> It's not either's first "First TIme" but it is the first together.  
> Basically just the missing scene in The Gang Misses the Boat.
> 
> Warning for (not super explicit) smut.

The kissing is going on longer than expected. It's not usually Dee's thing, kissing the guys she brings around. It’s not really something Charlie does at all.  It's nice, though, somehow both comforting and electric.

Charlie's hands are all over her, like he's trying to experience as much as possible before the chance is over. Maybe he's just not sure what to do with his hands. He grips her ass and pulls a leg tighter around him, like he can't seem to get close enough to her. His fingers slide up her back, grazing bare skin. Dee pulls back, breaking the kiss.  

They stare at each other, breathing hard. The taste of the other's mouth still fresh. His hands have stilled, one resting on her thigh, the other flat against her back. She wants to be touched more. To see how far they can ride this wave of connection. Dee's hands slide to his lap, palming at his crotch. He's half-hard, but she already knew that.  

"Wanna do this?" She asks. 

He nods. Wasting no time, Dee reaches to unbutton her pants. She really hopes she's wearing sexy underwear. She doesn't expect Charlie to know the difference, but there's still a learned worry that he'll laugh at her.  

Charlie struggles to get his own pants off, while she does the same hovering above him. It'd be a lot easier for both of them if she climbed off him, Dee realizes, but she has no plans of doing that. He manages to succeed first, wriggling and lifting his hips as he pushes his jeans and underwear to his ankles. Dee grabs his shoulder to keep from tipping backwards, as she balances on one knee to pull her jeans off. 

Dee looks down at his cock in the small gap between them. She'd never wondered about his dick before, but she's pleasantly surprised. She lowers back into his lap, pressing against him, and rubbing to hardness. 

She places her hand over his, fingers brushing his dick, filling in the gaps between his own fingers. He looks down, almost in disbelief that Dee Reynolds is touching him like this. Charlie wants to pull his hand out from under hers. He's accustomed to his own touch and wants to enjoy the feeling of her skin on his shaft. She raises her hips, shifting her panties to the side. It's easier than trying to get those off, too. Instead of stroking him, she teases the tip against her exposed skin. Charlie still pulls his hand away, as she sinks around him. It's better than he expected. 

"Mmmm, that's good," Dee murmurs as she begins rocking. Charlie's not sure if she's talking to him, or just talking, but it adds a feeling of mental gratification to the physical pleasure. His hands return to exploring her body, slowly this time, savoring every detail. 

A thought occurs to Charlie. He realizes it's a little late, but asks anyway, to be safe. Maybe she forgot. "Do we need, uh, should I-" he starts.  

Dee shakes her head. The box is all the way in her room, in her bedside table. She's not going to go get one and break this moment; they probably wouldn’t get it back. She pulls her shirt off, dropping it on the couch, then runs a hand through her tousled hair.  

Charlie’s focused on her chest, watching the rise and fall. It’s only then does she remember that she wore her best bra. The one that makes her breasts look big and full and great. It was supposed to be just for her, to boost her confidence at def poetry. Instead, it helps her feel sexy as she bangs Charlie Kelly.  

Dee's much quieter than the girls in the videos he's seen. Exhaling soft breaths and moans, her eyes shut and lips parted. She hasn't stopped moving this whole time.  

He knows the girl is supposed to go first, but this has been going on for a while now, and Charlie's not sure how much longer he can wait. A part of him wonders how she's lasting this long. 

Dee repositions slightly, placing her hand low, using her fingers to rub herself. It's a little gross, he thinks, but Charlie can't bring himself to look away. Charlie hears a low whimper and his eyes snap up to her face, finding her eyelids squeezed shut, teeth biting her bottom lip.  

She looks better than those girls in the videos, too. When she shouts and begins rhythmically squeezing his cock, he lets go. Maybe she would've wanted him to wait longer, until she's finished coming while sitting in his lap. But, she technically got there first, and he decides that's good enough. She can be mad later if she wants. 

Dee rests her forehead against Charlie's, her half-clothed body pressing against the fabric of his shirt. She smiles weakly, awkwardness already setting in, "Maybe we have gotten weird.” 

**Notes for the Chapter:**

> I'm still not too convinced how I feel about the last line. I just feel like Dee would make some lame/nervous joke.  
> He's glad she said no to the question, but I couldn't fit it in smoothly. I just feel like that should be cleared up.   
> Also, I don’t have any reason for adding it other than wanting it to seem more realistic. 
> 
> I've already got several in mind, but if there's any "firsts" you'd like to see for these two, shippy or platonic, leave a comment or message me on tumblr


	3. First High

**Summary for the Chapter:**

> Dee and Charlie share a joint.

"I didn't see you in homeroom. Were you skipping?" 

Charlie slides up next Dee. They're leaning against the side of the school, by the parking lot. School had ended an hour ago, and there were practically no cars left. 

She closes her book to look down at him, the height difference exaggerated by her forced rigid posture. "I had a doctor's appointment. Mom didn't want me home with her, so she made me come here for the rest of the day." She sighs, exasperated. "Now I'm stuck here, waiting for Dennis to take me home." 

"Oh," he says.  

Dee thinks there's a hint of pity in his voice. She changes the focus of the conversation, "What are you doing here?" 

"Dennis brought Adriano and the cool kids to buy some weed. I didn’t feel like eating spiders or anything, so I got out of there." 

Dee wrinkles her nose at the thought. "What'd you do if there weren't any spiders around?"  

Charlie shrugs. "Sniff stuff. Maybe eat some dirt or something." 

Still gross. She'd like to think she's not that desperate to fit in. The physical reminder of the root of her unpopularity and ridicule makes her wince. She shifts slightly, causing her brace to squeak more and pierces her ears. It seems louder than usual, and she feels embarrassed. 

Charlie looks at her. Eyes soft and curious, no hint of maliciousness. "Does it hurt?" 

"Ugh, yeah. Especially now."  He's still looking at her, some force compelling her to continue. She never gets to talk about it. "That's where I was today. They poke at me like some sort of lab rat, then tighten a bunch of stuff on this thing-" she taps on a metal ring, "then just as I get used to it, I'm back starting over again." 

Charlie nods and starts digging in his bag. He pulls out a joint, "You ever been high before?" He grins. 

"No," she admits. She's been various levels of buzzed. Alcohol was nothing new to her. But not weed. Her dad had always called it a poor person's drug, much preferring ridiculously expensive liquors and the occasional line of high quality coke. Dee's not sure if she'd rather sound prudish or pretentious. Charlie doesn't seem to notice anyway.  

"Oh man, you gotta try it," he says. "It makes everything feel nice. It'll help with your back, too." He places the joint between his lips and continues digging until he finds a book of matches. Charlie lights the tip of the joint and inhales. He holds it out to her, lightly coughing. Dee looks at him skeptically.  

He extends it closer towards her. "It's better than beer or glue," he explains when she doesn't move. 

"You just had that in your mouth," she states.  

He looks down at the end of it, inspecting. It looks clean. His eyes meet hers again. "It's fine. It's no different than us sharing vodka." 

"It- that was all of us. It's different," she stutters. The four of them in the Reynolds' basement passing around a bottle felt different, less intimate, than just the two of them waiting outside the school.  

"Just try it, Dee. It'll help, I promise. And I'm not sick or anything." He's still offering, and it makes her feel good, being accepted.  

She takes his offer and inhales a hit, coughing harder than he did. Nevertheless, the smoke finds its way to her brain. A warm, fuzzy feeling begins to grow.  

Charlie laughs good naturedly, "The first hit's kinda rough sometimes." She tries again, more gently, and it's much smoother this time. He doesn't seem to care that she went twice before passing it back to him. With that nice feeling growing and spreading, and Dee can feel her mind and body ease.  

He takes it back, inhales another hit and grins goofily. His eyes look duller now. 

"Rats are pretty cool, y'know?" Charlie comments. No, she doesn't. "It's not so bad to be like one. They're smarter than dogs and can survive anything. Probably even, like, the end of the world." 

He's missing the point, but she lets it slide. The weed is making her too lazy to correct him. 

"Speaking of rats. Ronnie makes you do this, too?" Dee asks. Charlie tilts his head, curiously. 

"The spiders," she explains. "All that dirtgrub stuff. Isn't he supposed to be your best friend?" Ingrid Nelson is supposed to be her best friend, but that doesn't stop Dee from occasionally trying to bring her down, too. She inhales slowly this time, savoring the feeling and flavor of the smoke. 

Charlie shrugs. "Nah, he doesn't. But, it's easier I guess. He's who they all get weed from. I gotta be something, too." 

Dee hums in acknowledgement.  

"Was I right? Did it work?" He asks. "With the..." He gestures around her, actions filling in for words. 

"Yeah. It did. You were," she responds. There's an awkward pause, unsure of the protocol here. "Thanks." 

Charlie simply nods, clearly not doing it for selfish reasons. He finishes off the last hit, resting his head backwards. He begins tapping his fingers against the brick wall. Little patterns of sounds he does a lot. Probably subconsciously, Dee thinks. It's stuff teachers berate him for, for supposedly disturbing the class. It's never really bothered her before, but she finds it surprisingly comforting now. 

She feels light and floaty; the pain in her back is long gone, the feeling of nothingness almost in the past, too. Dee hears a noise and realizes it's her giggling.  

"What's so funny?" Charlie asks. 

"I don't know," Dee replies, but she can't stop. 

Charlie's amused smirk slowly turns into laughter, too. Suddenly, they're both standing there in the cooling air laughing at nothing. 

It's only been twenty minutes since he joined her, when they see movement on the horizon. Dennis is approaching with Ronnie at his side. They stop in front of the pair, glaring when he catches their giggling. "I told Ron I'd give him a ride home for hooking me up," he tells Dee. He looks at Charlie, "You too, Dirtgrub." He starts past them, shouting back, "Get in the car, dweebs." 

Dee and Charlie take one last look at each other, inciting a new fit of giggles, before following the others. 

**Notes for the Chapter:**

> I feel like Charlie wasn't looking for Dee, they just happened to be at the same time-same place
> 
> I wanted Dee to be reading a script for the school play, but that didn't flow as easily.
> 
> He usually gets high off glue, but I like thinking Mac gave Charlie the joint because he felt bad Charlie didn't want to be around those people.
> 
> I wanted Dee to complain about Dennis some, and that's what makes them laugh. But it felt off.


End file.
